Synthesis of Acetophenetidin

Topics: Acetic acid, Chemical engineering, Chemical reaction Pages: 2 (468 words) Published: February 27, 2007

Acetophenetidin can be formed through two methods, Williamson ether synthesis and amide synthesis. By working in groups of two we were able to complete both methods of synthesis routes. The end result should be the synthesis of a similar product, by verification between the two individuals.


Experiment and Observations
Amide Synthesis of Acetophenetidin

The Synthesis reaction began by removing the colored impurities from the p-phenetidine, accomplished by mixing with HCl and heating. The dark black solution is filtered through a gravity filtration system allowing the slightly pink liquid to pass through the fluted filter paper. This process can be slow to drain leave only the remaining insoluble impurities in the filter. Once the pure sample is collected the crystallization process begins. Sodium acetate buffer, to maintain a relatively constant pH and acetic anhydride is added to the solution of p-phenetidine in HCl. After mixing and boiling, the solution is placed on Ice where the Crystallization process begins. The crystals are collected in a vacuum filtration using a Buchner funnel. This is a faster method of filtration compared to gravity filters that was preformed early in the experiment. Once filtered & dried the slight pink, powdery, crude product of Acetophenetidin is formed.

Crude Product
3.68 g
Percent Yield:
Melting point:

By performing a few small test it is determined that ethanol is a good solvent for the recrystallization process. My partner uses the chosen solvent of ethanol where as the amide synthesis part is continued by using ethanol – water solvent. Both methods continue to remove organic impurities and recrystallize a pure product. A sample of crude product is dissolved using ethanol and set to boil. While boiling, water drops are added to watch for a cloudy appearance. This was a tricky task because the solution had a swirl, oil appearance with the water drops, which...
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